Acetic Anhydride → 4'-Chloro-2'-fluoroacetanilide

HRID 1811535Notes

Reaction equation

HRID 1811535 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH3:10][C:11](OC(C)=O)=[O:12]>CC(O)=O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11](=[O:12])[CH3:10])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 8531744'-Chloro-2'-fluoroacetanilide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-chloro-2-fluoroaniline (50.0 g, 344 mmol) in AcOH (30 mL) is added Ac2O (60 mL) and the reaction is stirred at room temperature for 2 hours. The mixture is poured into ice water (500 mL) to give a solid precipitate. The mixture is stirred for an additional 1 hour at room temperature. The solid is filtered and washed with water and hexanes, then air dried to give N-(4-chloro-2-fluorophenyl)acetamide.

Workup

  1. customto give a solid precipitate
  2. stirringThe mixture is stirred for an additional 1 hour at room temperature
  3. filtrationThe solid is filtered
  4. washwashed with water and hexanes
  5. customair dried

Sources & evidence

ORD record
ord-fc9faf2c11f949529b35386960d7bdad
Source dataset
uspto-grants-2013_01
Patent number
US08362294B2

Reaction notes

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